Triethylamine → benzyl 4-amino-1H-pyrrolo[3,2-c]pyridine-1-carboxylate

HRID 875399Notes

Reaction equation

[NH:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1.C([N:12](CC)CC)C.Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]>ClCCl>[NH2:12][C:5]1[C:4]2[CH:3]=[CH:2][N:1]([C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])[C:9]=2[CH:8]=[CH:7][N:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 1H-pyrrolo[3,2-c]pyridine (500 mg, 4.2 mmol) in dichloromethane (6 mL), triethylamine (1.2 mL, 8.4 mmol) was added. The mixture was cooled to 0° C. and benzyl chloroformate (1.6 mL, 50% solution in dichloromethane, 4.6 mmol) was added drop wise. After complete addition, the reaction mixture was stirred at room temperature for about 1 hour. On completion, the reaction was quenched by addition of saturated aqueous sodium bicarbonate solution and the organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum to afford benzyl 4-amino-1H-pyrrolo[3,2-c]pyridine-1-carboxylate (1 g, 100%) as viscous liquid.

Workup

additionAfter complete addition
customOn completion, the reaction was quenched by addition of saturated aqueous sodium bicarbonate solution
customthe organic layer was separated
washwashed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-7e67b754894b448abfebcd535dad2962
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08980911B2

Reaction notes

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